After the drive from New York to the East End, there’s no better feeling than checking into a posh hotel bursting with amenities. It’s more convenient and failsafe than Airbnb, and there’s no renter’s insurance or security deposits needed. So consider hanging your hat at one of the area’s many hotels or bed-and-breakfasts. From Montauk to Shelter Island, Southampton to Sagaponack, we’ve got you covered.
Gurney’s Montauk Resort & Seawater Spa has it all! More than 140 rooms and suites, a 2,000-foot private beach, five restaurants and bars, ocean-fed seawater pool…the list is endless. Whether it’s a one-bedroom suite or a deluxe, three-bedroom cottage featuring a full kitchen, there are many accommodation options available. The rooms feature hardwood floors, subway-tile bathrooms with rain showers, and vintage brass fixtures, making Gurney’s an inviting and relaxing place where you can be close to the bustle of Montauk but far enough away for a good night’s sleep. 290 Old Montauk Highway, Montauk. 631-668-3203, gurneysmontauk.com.
Fireplaces, comfy couches, luxurious soaking tubs, private rooftop patios—Bridgehampton’s Topping Rose House offers them all. Let’s not forget the famed Jean Georges restaurant located in the main building. Vaulted ceilings give suites the cozy feeling of home, while a heated outdoor pool is the perfect place to relax any time of year. 1 Bridgehampton-Sag Harbor Turnpike, Bridgehampton. Call 631-537-0870 or email [email protected]. toppingrosehouse.com.
Featuring “an Old World approach to hospitality,” The Bridgehampton Inn has been a staple of Hamptons hospitality since 1994. Each piece of furniture in the rooms has been chosen specifically to tell a story about the inn’s rich history. Clean and elegant lines and gorgeous artisanal details make the spaces familiar and inviting. The Inn doubled its size in 2015. As if that weren’t enough, the restaurant serves up delicious locally sourced fare for your dining pleasure. 2266 Main Street, Bridgehampton. 631-537-3660, bridgehamptoninn.com.
White Fences Inn is located between Water Mill and Southampton. The Parrish Art Museum is only a short walk away. A gourmet breakfast is served to guests at a communal table. Top quality Frette bed linens and a Serta iSeries mattress encourage deep slumber. But it’s truly the warm and welcoming hosts, Liz and Eric Brodar, that make White Fences feel like home. 371 Montauk Highway, Water Mill. Call 631-500-9013 or email [email protected] whitefenceswatermill.com.
Nestled in the heart of East Hampton village, Mill House Inn is known for its decadent breakfast and personal touches. “[All] of us love food and the magical way it can instantly make us feel at home,” say Gary and Sylvia Muller, the owners. “That’s why, if a guest mentions he likes a particular kind of omelet, chances are he’ll see it offered at breakfast the next day.” Not to mention the specialized personal assistants that will take care of your every need, from restaurant reservations to after-hours access to village boutiques. 31 North Main Street, East Hampton. Call 631-324-9766 or email [email protected]. millhouseinn.com.
For a touch of Old World luxury, you can’t beat The Baker House 1650 in East Hampton. From the building to the grounds, all of it is 17th Century Cotswold-inspired—in other words, think English Country Manor. The interior is filled with warm details like exposed wooden beams and lush upholstery. Most guest rooms feature wood-burning fireplaces, antique rugs, and wooden sleigh beds. But it’s the infinity pool and manicured English gardens, featuring 200-year-old wisteria, that really delight. 181 Main Street, East Hampton. 631-324-4081, bakerhouse1650.com.
Have dog, will travel? c/o The Maidstone is just the place for well-heeled pooches—and their owners, of course. This Scandinavian-inspired inn is well known for the vintage red bikes guests use to pedal around East Hampton village, and for the iconic front porch featuring an array of rocking chairs. For sun-and-sand worshippers, each room includes a beach-parking permit. But it’s the little things that make c/o The Maidstone feel like home: prepared picnic baskets upon request, backyard croquet, bespoke clogs and luxurious bathrobes. 207 Main Street, East Hampton. Call 631-324-5006 or email [email protected], themaidstone.com.
If rustic and quaint is your thing, try the Ram’s Head Inn on Shelter Island. Its location is off the beaten path, but manages to be in the thick of it all by providing easy access to both North and South Forks. A grand lawn—perfect for putting your toes in the grass—dotted with Adirondack chairs and hammocks leads to 800 feet of beach with complimentary kayaks, paddleboards and sailboats on offer. There’s even outdoor tennis and a regulation-size bocce court. Get there before they close for the season on October 22. 108 Ram’s Island Drive, Shelter Island Heights. 631-749-0811, theramsheadinn.com.
Located in the heart of Southampton village, 1708 House is an historic bed and breakfast with thoroughly modern accommodations. Each room or suite has a private bath, flat-screen television, WiFi, in-season complimentary beach parking passes, and central air. It’s perhaps the only B&B in the Hamptons that sits atop a museum-like cellar dating all the way back to 1684. But it’s the decadent breakfast that seals the deal. The 1708 house is a slice of history, but not at the expense of luxury or convenience. 126 Main Street, Southampton. Call 631-287-1708 or email [email protected], 1708house.com.
Clean, modern, homey—these all describe Shelter Island House, located on a quiet street a mere hop, skip and jump away from the famous Sunset Beach. Rooms feature Cote Bastide bath products, in-room snacks and beach towels. On-premises restaurant, bar and bakery take care of all your dining needs. A generous porch and Shelter Island’s only heated hotel pool make enjoying the idyllic grounds a no-brainer. 11 Stearns Point Road, Shelter Island Heights. Call 631-749-5659 or email [email protected], shelterislandhouse.com.
If you’ve taken the ferry from Greenport, chances are good you’ve driven past The Chequit. The interior has been completely renovated and the resulting rooms are elegant and simple: crisp white linens and floating bedside tables are some of the design touches. But what really makes The Chequit feel like home is its complimentary breakfast in bed featuring a hot beverage of your choice and a light bite in the comfort of your guestroom. Starting in November, The Chequit is only open on weekends. 23 Grand Avenue, Shelter Island Heights. 631-749-0018, thechequit.com.
As far as first impressions go, it’s hard to beat the North Fork’s Jedediah Hawkins Inn. The building was constructed in 1863 in the ornate Italianate style. The inn, surrounded by lush gardens and scenic views, is close to vineyards, beaches and the Great Peconic Bay. It even boasts a charging station for your Tesla. Each room features local art, a fireplace, Frette sheets and a pillow-top mattress. Oh, and for breakfast expect freshly baked bread. Best of all? There’s a speakeasy in the basement where you can enjoy local wines and spirits. 400 South Jamesport Avenue, Jamesport. Call 631-722-2900 or email [email protected], jedediahhawkinsinn.com.
Small, intimate and thoroughly unique, Blue Iris Bed & Breakfast boasts just three rooms. Each has a private bath with whirlpool tub and a gas fireplace. Located within a one-mile radius of the inn are six major North Fork vineyards. Beautiful and expansive gardens, rocking chairs and a fire pit will help you unwind after a long day of wine tasting. The building was designed to resemble a traditional farmhouse, but inside it contains all the modern amenities a guest could want. 1100 Skunk Lane, Cutchogue. Call 631-734-7126 or email [email protected], blueirisbedandbreakfast.com.
Located in the heart of historic Southampton Village, the Southampton Inn, a local landmark for three generations, combines casual Hamptons style with European comfort. The largest Inn in Southampton, it boasts 90 charming guest rooms with luxuries such as Tempur-Pedic mattresses, mini refrigerators and complimentary Wi-Fi. Plan intimate or grand events or relax with a book in the library with its classical music and roaring fireplace. Southampton Inn is also one of the few pet friendly hotels. 91 Hill Street, Southampton. 631-283-6500, southamptoninn.com.
If you’re out at the end of the North Fork, you’ll want to stay at the one of the Orient Inn’s five airy, spacious bedrooms, each with private bath. Come morning, guests enjoy a sumptuous breakfast, fireside, in the wood-paneled Dining Room – or they may take it al fresco in the gardens, patio, or on one of the wrap-around porches. Guests may also take their breakfast to their rooms. 25-500 Main Road, Orient. 631-323-2300, orientinn-ny.com.